


The ABC's of Destiel

by captaindestiel1



Series: Destiel multi-chapter AU stories [6]
Category: Supernatural
Genre: ABC Challenge, Alpha Dean Winchester, Alpha/Beta/Omega Dynamics, Alternate Universe - Bar/Pub, Anal Fingering, Anal Sex, Angelic Grace, Asphyxiation, Autoerotic Asphyxiation, Begging, Biting, Blindfolds, Blood Drinking, Blood Kink, Blow Jobs, Blow Jobs in a Car, Bottom Castiel, Bottom Dean Winchester, Castiel and Dean in Love, Castiel is a Tease, Choking, Church Sex, Claiming Bites, Cock Slut Dean, Come Eating, Come Swallowing, Coming In Pants, Coming Untouched, Consensual Underage Sex, Cowgirl Position, Daddy Castiel, Daddy Kink, Danger, Dean Winchester is Castiel's Son, Dean in Panties, Desk Sex, Dirty Talk, Doggy Style, Dom/sub Undertones, Established Castiel/Dean Winchester, FBI Agent Castiel, FBI Agent Dean Winchester, Face-Fucking, Father-Son Relationship, Father/Son Incest, Grace Bondage, Grace Bonds, Grace Kink, Grace Sex, Guard Dean, Handcuffs, History Teacher Castiel, Horny Castiel, Horny Dean, Impala Sex, Implied/Referenced Rape/Non-con, Kept Boy Dean, Kitchen Sex, Kneeling, Knife Play, Leather Kink, Leather Trousers, Light Bondage, M/M, Mates, Mildly Dubious Consent, Multiple Orgasms, Office Sex, Officer Dean, Omega Castiel, Oral Sex, Orders, Orgasm Control, Orgasm Delay/Denial, Orgasm Denial, Panties, Police Officer Dean, Possessive Castiel, Priest Castiel, Priest Kink, Prison, Prison Sex, Prisoner Castiel, Prostitute Castiel, Public Sex, Punishment, Rimming, Sam Is Scarred For Life, Sam Is So Done, Semi-Public Sex, Sex Toys, Sex in the Impala, Shameless Smut, Sleep Sex, Sleepy Cuddles, Sleepy Sex, Slut Dean, Smut, Spanking, Sweet, Teacher-Student Relationship, Teasing, Teen Dean Winchester, Top Castiel, Top Dean Winchester, Twink Castiel, Twink Dean, Underage Dean, Underage Sex, Vampire Dean Winchester, Vibrators, Wake-Up Sex, Young Dean Winchester
Language: English
Status: In-Progress
Published: 2015-08-08
Updated: 2016-04-12
Packaged: 2018-04-13 13:44:18
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Underage
Chapters: 21
Words: 11,310
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4524243
Author URL: https://archiveofourown.org/users/captaindestiel1/pseuds/captaindestiel1
Summary: <blockquote class="userstuff">
              <p>The ABC's of Destiel. i want to write a separate drabble for each kink beginning with a letter of the alphabet. (so 26 drabbles lol)</p><p>examples:<br/>B-bondage, D-daddy kink, S-somnophilia ect.</p><p>Some of these kinks are some of my own and some are suggested by friends. so if i dont do some of the kinks properly i apologize, hope you like them anyway :);</p>
            </blockquote>





	1. A is for Asphyxiation

**Author's Note:**

> asphyxiation is a noun that means the condition of being deprived of oxygen.

To be honest it freaked Cas out when Dean asked him to well...

Castiel applied more pressure and a harsh gasp escaped the hunters throat. It took Cas a few tries to get over the squeamish bit of it.

_"C-Cas?"_

_Blue eyes flicked up and the angel smiled at his lover. "Yes Dean?"_

_"H-Have you ever heard of auto-erotic asphyxiation?" Dean squirmed in his seat and his face turned red._

_"Could you elaborate?" Castiel set his coffee down. Dean continued to squirm in his seat, eyes downcast and his face getting redder. "Dean." Castiel touched Dean's face and pulled him into a deep kiss. "You can tell me anything, you know that." Dean felt safe around Cas, he always did._

_"I-I want you to choke me when we have sex." Dean mumbled out and Castiel's eyes widened. Once the angel understood he smiled and kissed Dean's head._

_"Anything you want babe."_

More surprising to himself Castiel kind of liked this. He liked having Dean's life at his hands, to be in control. The hunter's face had become red, his beautiful green eyes fluttering as he tried to breathe against the pressure. As Castiel pushed hard on Dean's windpipe the hunter tried to moan, bucking his hips up and clawing at the sheets. Dean's dick was raging red, throbbing against his stomach as Castiel tested the pressure on Dean's neck, letting up to give Dean some air.

"F-Fuck Cas." Dean coughed out as he caught his breath, Castiel giving lazy thrusts into his lover until Dean nodded for him to go again. Castiel's hands quickly went to Dean's throat again. A few seconds following Dean came hard, choking out his orgasm. Castiel released Dean's throat, thrusting harder until he reached his own.

"Damn." Dean choked out, his voice was wrecked.

"That scared the hell out of me Dean." Castiel sighed, collapsing on his hunter. It was kind of hot, but it still worried Castiel. "What if one day I linger too long and you die?"

"It's okay Cas." Dean's laugh was like sandpaper. "If you kill me you can bring me back."

"That's not funny Dean!" Castiel slapped Dean on the back of his head and the man winced.

Dean laughed off the smack and pulled Cas in close. "It's okay Cas, I trust you. I know you won't let me die."

Castiel huffed "Damn right I wont."

"Can we do it again?"

"Sure."


	2. B is for Bondage

**Summary for the Chapter:**

> bondage: sexual practice that involves the tying up or restraining of one partner.

Dean yanked at his handcuffs making sure they were fastened properly as his lover crawled on top of him. There was a cuff on each wrist and each ankle, chained to each bedpost. Now if there was one thing Dean loved in the bedroom it was being helpless. Normally Dean was all fight and in charge but in the bedroom he wanted to be tied down and controlled. And who better than his powerful angel lover tying him up.

"Are they too tight?" Castiel purred into Dean's ear.

"Nah they're perfect." Dean smiled as Castiel pressed a gentle kiss to his lips.

"Good." Castiel smiled as he blindfolded Dean. The blindfold was something Dean has slipped into the shopping basket Castiel was carrying while they were shopping for condoms. When he spotted the blindfold Castiel wasn't the least bit shocked, Dean was always throwing new things for the bedroom when Cas wasn't looking. Not that the angel minded.

Dean let out a shiver as Cas left open mouthed kisses trailing from his neck, down his torso just to where Cas's nose grazed the base of Dean's length. Dean let out a sharp breath as Cas flicked his tongue across the slit, fingers teasing at his balls. The best part about the blindfold was that he never knew where the angel would touch him next.

Dean bucked up, the cuffs keeping him forced to the bed. "Fuck. Fuck. Cas." Dean squirmed under Castiel's careful attention when the angel took Dean full force to the back of his throat. When Castel hollowed out his cheeks and swirled his tongue around the head, Dean gave a long moan that descended into a whimper. Castiel teased him for what seemed like hours, careful flicks of the angel's tongue were driving him wild. Dean wanted nothing more than to free his wrists, grab the angel's hair and thrust up into his mouth. 

The hunter tugged at the cuffs until they left deep welts in his wrists and ankles. Then Cas did that thing, the thing that always drove Dean insane. He started humming. A litany of "Fuck. Ohs." and "Cas" dripped from Dean's lips at he came down the angel's throat.

"F-Fuck." Dean gasped out as Castiel unlocked the handcuffs and removed the blindfold.

"Was that fun?" Castiel smiled.

"Was awesome." Dean grinned, rubbing the sensitive skin on his wrist, smiling when the angel pressed a gentle kiss to the welts.


	3. C is for Chrematistophilia (paying for sex)

**Summary for the Chapter:**

> Chrematistophilia - Having to pay for sex or having a sex partner steal from them, being robbed

Dean scoured the bar, looking for pretty much anyone willing to fuck. He spotted a few easy sorority girls that had been staring at him all night, a big burly looking guy that Dean wasn't in the mood for tonight and a cougar that had dyed her hair so many times it was practically white.

"You come here often sweetheart?"

Dean quickly turned to the previously empty seat next to him to see a holy-fuck-blue-eyes-breath-taking-younger-man now in it's place. He looked maybe in his early twenties, had near raven hair and a cut but smaller frame than Dean.

"Sometimes, you busy tonight baby?" Dean put on his best flirty smile, hand grazing over the younger man's and fuck he was so soft.

"Depends." The younger smiled, pulling Dean's hand up his lips and giving a quick swipe of his tongue across the other man's fingers and Dean let out a shiver. "How much money do you have?"

Fuck. Oh holy fuck. A hooker, this beautiful man was a hooker. Fucking score of the century. Now Dean was weird, to be honest it turned him on to have to pay for sex. Made zero sense to him but for some reason he found it very hot. Dean himself was extremely beautiful, broad chest, forest green eyes and clean cut gorgeous hair. He could get anyone he wanted but for some reason paying for it turned him on.

"How much you charge?" Dean purred, leaning in to the other man's ears to keep their conversation private. Prostitution wasn't exactly legal and he'd be damned if he let a gorgeous thing like this get away.

"$200 for everything." Dean let out a long whistle like the price was too high. He was playing of course, guy this beautiful could probably charge a thousand and Dean would still fuck him.

"Little cheap don't you think sweetie?" Dean teased and the other smiled.

"Im giving a discount, not everyday I get such a handsome client."

Dean wasn't sure if that was special for him or if this guy was just good at his job and trying to woo him. Either way, $200 to hit that? Hell yes. Dean looked like he was thinking it over, even though he had decided already. "Hmmm two-hundred." Dean gave a smirk "Alright, let's get out of here-"

"You can call me Castiel." The other man smiled.

"Dean." The green eyed man smiled back.

Castiel smiled, grabbed Dean's hand and pulled him out of the bar. The two arrived at the motel Dean was staying at in record time. Within seconds of the door closing Castiel was on his knees, unbuckling Dean's pants.

"F-Fuck." Dean braced himself against the dirty motel wall, trying to keep himself up as Castiel took Dean to the back of his throat immediately. Damn this guy was good. Castiel hollowed out his cheeks to take Dean in even further and started humming. Dean's hand instantly tangled in Castiel's hair and started thrusting his hips forward. He could have sworn he heard Castiel choke and pulled back.

"You alright Cas?" Dean's dick twitched when electric blue eyes looked up at him, a mix of precum and drool dripping from Cas's full lips. 

"I'm fine baby." Castiel smiled, rising up to pull Dean into a deep kiss, his tongue pushing past Dean's teeth and licking at the roof of his mouth. Dean let out a groan as Castiel pushed him from the wall to the bed, nearly tripping over his jeans around his ankles.

"What do you want me to do gorgeous?" Castiel purred, having ridded Dean of the rest of his and Dean's clothes, straddled in his lap as Dean caught his breath.

"I want you to ride me Cas." Dean gave a predatory smiled and Cas returned it with almost a sweet one. Deans dick twitched in impatience as Castiel worked himself open, after a few minutes Dean's impatience got the best of him and he yanked Castiel's fingers free. Castiel almost looked offended but kept his work face on.

"You got a condom?" probably something Dean should have asked before they got to this point. Castiel nodded, clambering off Dean to grab a condom and lube from the pocket of his own discarded jeans. Dean's eyes fluttered as Castiel slipped the condom on Dean's painfully hardening cock. Dean left out a satisfied moan as Castiel sank down on his dick.

"Fuck, Cas. You're still so fucking tight." Dean let Castiel take control for a while, tortuously rotating his hips expertly but slowly and it was driving Dean insane. Castiel let out a noise that was half yelp and half moan and Dean gripped his lithe hips and gave a harsh thrust up into him. As Dean pushed up harder he changed angle, hitting Castiel's prostate head on. Castiel was letting out the filthiest string of moans that Dean could have sworn were genuine. It wasn't long before Castiel was clenching around him, soft hands braced against Dean's broad chest. 

"Fuck. Oh god. _Dean._ " Castiel whined, throwing his head back.

"Fuck. Fuck. Fuck. Cas!" Dean screamed out his orgasm as he released inside Castiel. Dean laid there spent as Castiel bobbed on his softening dick and cumming untouched on his stomach with a harsh "Dean." escaping his throat.

Once cleaned off, Dean reached for his wallet as Castiel slipped his jeans on.

"Here you go sweetheart." Dean handed Castiel two crisp hundred dollar bills. Castiel took the bills and handed one back to Dean, a look of confusion across the older's face.

"That was a damn good fuck." Castiel smiled, pocketing the other bill. "Next time you're in town, you can fuck me for free." Castiel winked before leaving the motel room, Dean collapsed on the bed. He would have to visit this town more often.

**Notes for the Chapter:**

> this one was weirdly long lol.


	4. D is for Daddy Kink

**Summary for the Chapter:**

> Daddy kink- Where during sexual intercourse the male is being aroused when their partner or corresponding male called him "daddy" In some cases it is in the literal sense.

**Notes for the Chapter:**

> Don't judge me lol.
> 
> Btw they are actually related here and underage but it's consensual. Edit* I decided to make Dean Castiel's adopted son just to make it a bit more comfortable for most readers. Hope you still like it :).
> 
> Enjoy :).

"D-Daddy please." Dean whined pressing back on his father's fingers so they would go in deeper.

"Shhh." Castiel ran a rough but comforting palm against the small of Dean's back. "Don't worry baby boy, daddy will give you what you need."

Dean whined as he insistently pushed his ass back further, crying out when the pad of Castiel's finger brushed his prostate. Now if there was one thing Cas was going to hell for, it was fucking his fifteen year old son. Well adopted son but still. However for him and Dean this was completely normal. It had all started when Dean was twelve, he had given his father a blowjob in his sleep and Castiel wasn't going to deny his baby boy anything, even him. Sure it was wrong but Castiel knew he would never love anyone but his son and he hoped Dean felt the same way.

"Dad...Daddy..." Dean panted out as Castiel gave torturously slow strokes inside Dean, purposefully aiming for that sweet spot. 

"Yes sweetheart?" Castiel purred, palming himself through his jeans as he watched his young son writhe under his careful attention.

"Please...want you." Dean gasped out, whining into his pillow as his dick strained for attention, momentarily humping the mattress to get some relief. Dean let out a sharp breath as Castiel pulled his fingers free, a rustling of denim behind him.

"Is this what you want?" Castiel growled as he teased Dean's slick hole with his dick. "Daddy's cock in your ass?"

Dean let out a high whine as his father applied pressure to the ring of muscle, the head slightly teasing Dean.

"Yes daddy. Please, I'm such a slut for your cock, for you. Please."  Dean begged, a litany of "Daddys" and "Please" fell from Dean's lips as Castiel continued to tease him.

"That's my good boy." Castiel praised him as he pushed past Dean's entrance, releasing contented sigh as he nestled himself deep inside his son.

"Fuck. Daddy you feel so good. So full." Dean sighed, content as Castiel began to rock his hips. Dean let out small pants as Castiel pressed his chest to his back, it was warm and comforting and Dean pushing his ass back to try and get his father to move.

"How do you want me to fuck you baby?" Castiel purred into Dean's ear and a shiver ran down the younger's spine.

"Hard Daddy. Fuck me hard, please." Dean's voice cracked and Castiel smiled. 

"Anything you want babe." Castiel pulled back, hands going to Dean's lithe hips and immediately setting a punishing pace.

"Fuck. Fuck. Daddy, yes. Fuck me, pound my slutty hole. Such a slut for you, just for you daddy." Dean whined, clawing at the sheets as his cock bounced with every forward thrust from Castiel.

"Thats right-ngh-just for me baby boy." Castiel shifted angle and Dean let out a loud moan. "My Dean. Mine. Mine." Castiel was always possessive over his son and to be honest it made Dean feel loved. He was Castiel's and no one elses.

"Da-Daddy, I'm so close." Dean panted out.

"That's it, cum for me baby boy." Castiel slipped a hand around Dean's waist, a few quick tugs before Dean came apart under him, spilling all over Castiel's hand. Dean always came first, Castiel made sure of that. Castiel continued thrusting, his son pliant under him, still riding out his orgasm as Castiel reached his own.

"Daddy." Dean purred out, his voice a little rough.

"Yes honey?" Castiel smiled as he wiped his son clean with a warm rag.

"I love you." Dean placed a gentle kiss on his father's scruffy cheek.

Castiel smiled at his beautiful son before placing a chaste kiss to his full lips. "I love you too baby boy."


	5. E is for Edging

**Summary for the Chapter:**

> Edging- getting super close to orgasm but stopping and either stopping a few minutes and build the orgasm again or stay close for a long time

Dean's breathing was hitched, his muscles ached and little whines escaped his throat. "Cas. Cas please." Dean begged, a whimper in his throat.

"Not yet Dean." Castiel smirked as he slipped a third moistened finger inside Dean. This had been going on for hours, Castiel bringing Dean to the edge and yanking him back again. Used toys littered the floor as well as multiple packets of lube were scattered across the bed. Castiel himself had came seven times already and Dean whined everytime he did.

"Cas...p-please." Dean arched his back as his abused overly sensitive prostate was brushed again. Castiel teased a finger over the cock ring that was keeping Dean from his release and the younger man jolted up.

"No Dean. Not yet. Now be still." Castiel ordered and Dean let out a gasp as Cas teased his tongue over the slit of his dick. His whole body was flushed, his dick aching and his whole body dripping in sweat.

"So good Dean. So beautiful." Castiel pulled his fingers free and Dean whimpered at the emptiness. Castiel's fingers were replaced by a buzzing pink vibrator that was kicked on high the moment it was inside Dean. High pitched moans escaped Dean's throat as the vibrator buzzed inside him. After a few minutes of Dean thrashing on the bed Castiel spoke as he stroked his own dick "Do you want to cum Dean?"

"Yes." Dean gasped out.

"Do you want me inside you?"

"Fuck yes. Please. Please. Fuck me Cas. Let me cum, Please." Dean had never said the word 'please' so many times in his life.

"You can cum after I do." Castiel pulled the vibrator free, replacing it with his dick as he slowly pushed into Dean. Castiel slid in without much effort, Dean was stretched from all the teasing, over sensitive from the attention. Dean gave a small cry as Castiel began to thrust into him. They were slow thrusts, but they were enough to bring Dean to the edge again just waiting to be tipped over.

"Damn Dean. You're so warm." Dean clinched best he could around Castiel in an attempt to get him to cum. Much to Dean's relief Castiel moaned when he felt him clinch, spilling into Dean. As Castiel was coming down from his high, Dean pawed at his arm in an attempt to get his attention. "Hmmm?" Castiel turned his attention to his now teary eyed lover and smiled. "I'm going to take the ring off now Dean. Don't cum until I say so. Okay?" Dean nodded furiously and Castiel removed the ring. His fingers brushed Dean's dick as he pulled it off causing him to take everything he had not to lose it. 

Castiel leaned into Dean's ear and whispered. "Cum."

Dean came with a shout then blacked out. Best orgasm of his life.

"Dean?"

Dean blinked his eyes open to see a smiling Castiel hovering over him. "You okay?"

"Yeah babe." Dean gave a weak smile and sat up as Castiel gave him some water.

"You wanna do that again sometime?"

"Hell yes." Dean gasped out as he caught his breath.


	6. F is for Face-fucking

**Summary for the Chapter:**

> Face-fucking: Sliding your cock in and out of someone's mouth usually while holding their head still or moving it in opposition to the movement of your hips.

**Notes for the Chapter:**

> Guys i need feed back so i know people are ACTUALLY reading this lol. Otherwise i feel like i'm writing to a blank wall XD.

Castiel let out a deep moan as Dean licked at the head of his dick. 

"Damn Cas, you taste so good." Dean smirked, green eyes flicking up to meet Castiel's blue.

"You want it?" Castiel teased, rubbing his dick across Dean's full lips.

"Fuck yes." Dean breathed out, wincing as Castiel tugged at his cropped hair. If there was one thing Dean loved more than Cas, it was the angel's dick. Dean wasn't sure if it was because Cas was an angel or what but he tasted good, sweet, so fucking sweet. Dean was pretty sure that Castiel used his grace to make his dick taste like apples on purpose or something.

"Open your mouth." Castiel commanded. Dean licked his lips before obeying, opening his mouth as wide as he could. Castiel gave another tug at Dean's hair before thrusting all the way back to his throat, making the hunter gag. Fucking gag reflex, Dean figured at this point he would be rid of it, not that he didn't kind of like choking on Cas's dick a little. Maybe a little.

Castiel let out a contented sighed, throwing his head back as Dean's warm mouth enveloped him. Dean started moaning, his eyes fluttering as his throat relaxed. Castiel returned his attention to Dean who was still moaning around his dick. "Breathe through your nose Dean." was all the warning the hunter got before the angel pulled back, nearly pulling his dick all the way out before harshly thrusting to the back of the hunter's throat. Dean held back a cough, breathing through his nose as his angel instructed. Dean just sat there on his knees, letting Cas use him. Dean tried his best to swirl his his tongue around Cas's dick but the thrusts coming from the angel were to hard and erratic. Dean just moaned while Cas fucked his mouth.

Castiel looked down to see Dean reaching for his own dick, give it slow strokes waiting for Cas to give him some kind of permission. "Go ahead Dean." Castiel slowed his pace as he spoke, picking it back up immediately after. Dean whined around Cas's dick as he was close to orgasm. The angel was grunting now, his hips stuttering before cumming down the hunter's throat. A few fevered strokes later Dean came hard, sighing as he came down from his climax. Dean pulled his lips off Castiel's softening dick, gulping down the angel's release. 

"Hey Cas?" Dean stood up to pull the angel into a deep kiss, Castiel returning the advance by licking at the roof of Dean's mouth and tasting the remains of his release. 

"Mnnnn?" Castiel hummed through the kiss, arms snaking around the hunter's waist.

"Did you know you taste like apple pie?"

Castiel smirked, a mumbled. "uh huh." before claiming Dean's lips again in a deep kiss.

**Notes for the Chapter:**

> Yeah Dean. Apples. That's your excuse. To me this sounds like a real life Dean excuse.
> 
> Sam: Dean you sucked Cas's dick?!
> 
> Dean: In my defense Sammy, it tasted like apple pie.
> 
> *Cas in the background trying not to grin like an idiot*


	7. G is for Grace Sex

**Summary for the Chapter:**

> Grace sex- An angel using their celestial powers or "Grace" to sexually stimulate a person without actually physically touching them.

Research. Fucking research is Dean's least favorite thing in the entire world. Book after book, page after page felt like it was just ebbing Dean's life away. Dean jumped as he felt something in his shirt and shiver ran down his spine. Okay that was weird. Dean returned to his book, the words were all starting to run together. Dean yelped as he felt something warm and wet flick across his nipple. What the fuck?

"Dean are you okay?" Sam cocked his eyebrow, attention moved from his book to Dean.

"Uh yeah. Cold chill." Dean gave a nervous laugh, flinching when the feeling came back again, this time traveling up his chest to flick both nipples. It almost felt like...a tongue. Dean patted his shirt, nothing there. He looked up at a small chuckle that came from across the table, the source of the noise was an angel with his nose buried in his own research. Dean stared hard at Cas, almost positive that the angel was responsible for whatever the hell was going on. Dean tensed as he felt a pressure on his now half hard dick, his hairs on end. The pressure began to glide up his dick and Dean let out a loud moan.

Sam's eyes flicked up, a suspicious glance at his brother. "Dude what is wrong with you?"

Dean gulped, breathing as the pressure disappeared. "Just cramped up from all this uh research." Sam raised an eyebrow. "And I'm hungry."

"I'll go get us some food in a minute Dean." Sam huffed, irritated that he kept getting interrupted.

The pressure came back, now both on Dean's dick and his chest. Something almost like a feather ghosted across Dean's lips. Castiel was smirking at his book across the table like it had told him the best joke in the world. "Cas what a-ah!" Dean whined out as he felt something warm pressing against his entrance, probing it ever so slightly.

"Fine I'll go get us some food." Sam huffed out "You don't have to whine Dean." Sam stood up grabbing his coat. The pressure against Dean was being more forceful, pushing further into him as it continued to stroke all over his body. It took everything Dean had not to give a loud moan. Once he heard Sam slam the bunker door behind him, Dean glared at the angel who was now full on grinning.

"Cas...What the fuck?" Dean growled, flinching as the force pushed deeper into him.

"I wanted to touch you Dean." Castiel stated in a matter-of-fact tone.

"Maybe you could have _actually_ fucking touched me." Dean hissed out as the force stroked his dick faster, back arching in the chair.

"Sam was here." 

"Well he's-ah-not here now." Dean gave a weak smirk.

"Does it feel good?" Castiel asked, ignoring Dean's comment. 

Dean let out the moan he had been holding in before answering. "Yes." the force teased the head of his dick and his pants were way too damn tight. "How the hell are you doing that?"

"My Grace." Castiel answered as he got up from his chair to sit on the desk in front of Dean. The hunter tried to reach up to touch his angel, growling in frustration as his arms were forced down to the arms of the chair by the grace.

"Just be still and enjoy it Dean." Castiel added a small amount of force of his grace to drive his point home. " _Fuck it."_ Dean decided leaning back in the chair as the grace resumed its work. Dean gasped as he was stretched out again, his dick straining against his jeans. The angel gave a flick of his wrist and the grace expanded inside Dean causing him to cry out.

"Fuck. FUUUCK." Dean howled out as the grace abused his over stimulated prostate. A few minutes later Dean flinched as Castiel wiped drool off the corner of the hunter's mouth.

"Feel that good Dean?" Castiel teased, thumb now grazing over Dean's parted lips.

"S-Shut up." Dean blushed, moaning as the grace swiped across his prostate again. It was relentless, electricity shot through Dean's body and he came in his pants. Like a fucking teenager.

As Dean came down from his high, his blissed out expression turned to irritation. 

"You could have at least taken my pants off."

"Nah i like you dirty." Cas laughed.

"That so?" Dean licked his lips and Castiel blushed.

"Wanna go have actual sex now?"

"Fuck yes." Dean smirked, his dick bouncing back like a champ.

The moment Sam came back with food he rushed back out the door at the first "Fuck me angel" echoing through the bunker.

**Notes for the Chapter:**

> I freaking love Grace sex.
> 
> and traumatized Sam. Traumatized Sam is the best.


	8. H is for Hematolagnia (blood kink)

**Summary for the Chapter:**

> Hematolagnia-A sexual fetish for blood which evokes arousal when present on the fetishist’s sexual partner, especially if nude. It is often accompanied by licking or drinking blood through bloodletting or biting,

Castiel was panting. Freaking panting. Five vamps, twelve, a hundred, Castiel had lost track of how many he had killed. At the end of this slaughter was Dean, hopefully it was still his Dean. Castiel approached the hunter jumping back at a hiss he received. Dean was baring fangs, _fangs_. Castiel's face fell Dean hissed at him again, his eyes rolling in the back of his head when Castiel touched his forehead, knocking him out with his grace.

Dean awoke in the dungeon of the bunker, chained to a chair. "CAS!" Dean screamed out, eyes flicking to a dark corner where the angel had previously been hidden. Castiel was littered in cuts and bruises, a deep cut on his cheek was dripping blood, Dean licked his lips at the sight. Castiel hadn't really thought about healing himself he was entirely too focused on Dean.

"Come here Cas." Dean smiled, his fangs were retracted. The angel stepped forward but out of Dean's reach. "Does it hurt?" Dean's voice was soft, just like usual, just like Dean. Dean's eyes flicked to the floor where Cas's hand was dripping blood. Dean's muscles tensed and a primal growl rested in his throat. "Come on Cas, unchain me. It's Dean, _your_ Dean."

Without thinking Castiel loosed the chains and straddled his lap, happy to be close to Dean again. "I shouldn't be doing this." Castiel sighed, flinching went Dean licked the drying blood on his cheek. "Dean?' Castiel looked down questioningly as his lover was now licking his lips.

"You taste divine angel." Yup totally Dean, cheesy one-liner Dean. Castiel nearly forgot Dean was currently a vampire until he licked more blood dripping from Castiel's neck. The angel let out a low moan as Dean brushed his tongue up his neck to his ear.

"Does that feel good angel?" Dean purred, rocking his hips, his lover feeling his erection straining against his own. Castiel hissed against the friction as Dean continued to lick him, until nearly every drop of blood was gone, the vamps dick now straining against his jeans.

"D-Dean." Castiel sighed as Dean's lips ghosted over his neck, searching for more. 

"You taste good Cas. So good." The angel let out a pained yelp as fangs dug harshly into his neck.

"Dean...S-Stop." Castiel clawed at Dean's back, trying to pull back but the fangs were latched to his neck like a vice.

"Dean stop!" a bright light filled the room, forcing Dean back, nearly ripping Castiel's neck. Blood practically poured from the angels neck. Once Dean had regained his footing he was on the angel again, knocking him to the ground. "Dean, sto-ah." another swipe of Dean's tongue against Castiel's neck, hands to the angel's wrists and pressing his erection hard against Castiel's own.

Within minutes Dean's was sucking at Castiel's neck again, lazily thrusting into his lover. Castiel was feeling weak, maybe it was his vessel's extensive blood loss. Castiel gave a weak moan as Dean shifted angle, hitting that sweet spot that was driving him insane. Castiel came with a hoarse cry, Dean still latched to his neck as he spilled inside his angel. 

Castiel blacked out from blood loss, a strange thing for an angel, maybe the vampire was draining his strength. The angel's eyes eased open as he found himself in Dean's bed, a gentle kiss was placed to his forehead.

"Good night Cas." With bleary vision, Castiel watched as Dean left the room.

 

**Notes for the Chapter:**

> You can say a vampire is cheating. cause it is. but lets count it lol.


	9. I is for Imprisonment

**Summary for the Chapter:**

> Imprisonment, other (see Prison scenarios). kind of a kink sort of lol.
> 
> i found it on a kink list. 
> 
> the letter I is hard lol.

"Line up!" Officer Winchester barked and the inmates stepped out from their cells. Dean Winchester was known as the toughest guard of purgatory prison and the warden. Dean was beautiful, strong and _deadly_ , no inmate dared to talk back to him. At least not more than once. Dean inspected each inmate, he stopped at a raven haired prisoner who had his head lowered but blue eyes looked up at the officer through thick lashes.

"Novak." Dean growled out.

"Yes sir?" Novak held back a smirk, trying not to let the rest of the prison in on his and the warden's dirty little secret. To be honest, they had already guessed when the warden threatened them under pain of death if they ever touched Novak.

"Look at me." Dean ordered, placing his night stick under Novak's chin so blue met green. "My office. Now." A almost high school like "ooooo" came from the other prisoners and Dean shut them up with a steely glare.

Novak followed Dean a few feet back until they reached his office. As Dean made sure the door was locked, he pulled Novak into a deep kiss, shoving him against the wall.

"Castiel." Dean breathed out, hand quickly going to unbutton the prison jumper as Novak moaned against his lips. "Cas." Dean breathed out.

"Dean." Castiel moaned out as the jumpsuit was slid off his shoulders.

This had been going on since Castiel's third day here. He had been taking a shower by himself, long after the other inmates had left. When Dean walked in to make sure the shower was clear he froze to the spot. One look at Cas's naked body, then his eyes and it was like electricity shot through both of them and they were on each other within seconds.

Castiel continued to moan as Dean kissed along his neck. Now Castiel had been expecting the worst in prison. Beatings, rape, hard work. But belonging to the warden, loved by the same man just made prison like a high security daycare for Castiel. "Miss me baby?" Dean purred into the inmate's ear as he palmed his crotch. This was the weirdest relationship. Sure they liked to play, use Deans handcuffs but it was...love.

"Mhmm." Castiel purred back, ridding Dean of the top half of his uniform. "You smell so good." Dean smelled like whiskey and aftershave, it was intoxicating. 

"You in the mood to play?" Castiel flinched as the cold steel of Dean's handcuffs clicked across his left wrist.

"Yeah." Castiel pressed a smiling kiss to Dean's lips as his arm twisted back behind him as the other clicked behind him.

"Now." Dean flipped Castiel around, bending him over the desk. "You have to right to remain silent." Dean pressed his clothed erection against Castiel's bare ass. "Anything you say and do will be held against you-"

"Dean." Castiel smirked and Dean pressed harder against him.

"Clever." Dean chuckled, unbuckling his pants and rubbing his dick up the cleft of Castiel's ass.

"Ready to do 'hard time' Cas?" 

Castiel held back a loud laugh, Dean was always so cheesy. The laugh turned into a moan as Dean began to press into him. Knowing this was coming, Castiel had opened himself up for Dean with some lube his lover slipped him last night. "You're so warm." Dean sighed, as he buried himself to the hilt. They laid like that for a minute, Dean had been away on leave and he missed Castiel.

Castiel gave a low moan as Dean gave shallow thrusts, his hands writhing behind his back as the cuffs tugged at his skin. Dean's hands moved to the chain of the handcuffs, using it to pull Castiel standing with Dean still inside him. "Nghhh." Castiel groaned, Dean's warm chest against his bare back. "Cas. Cas." Dean started chanting his name as he thrusted into him, a warm hand now braced to Castiel's chest for support. Castiel gave out small pants, his dick bobbing against his stomach.

" _Dean._ " Castiel moaned out, cumming when Dean gave him a few quick tugs. It had been far too long since Dean had touched him. A few quick thrusts later Dean came inside Castiel with his lover's name on his lips.

Castiel leaned his head back on Dean's chest and sighed. "I have to go back to my cell."

"I know." Dean mumbled, wrapping his arms around Castiel's chest

"I love you Dean."

"I love you too."

Only three more years.

**Notes for the Chapter:**

> how the hell did this end up so feely?! wtf brain?
> 
> Figured it was a good turn from usual prison fic, but i didn't mean for it to be that sweet lol.


	10. J is for Jump Start

**Summary for the Chapter:**

> Essentially wake up sex lol.

Dean's eyes eased open, blinking awake. He looked down to see Castiel wrapped around his leg, he looked so cute, like a lost puppy. Dean's breath hitched when Castiel pressed his morning wood against his thigh and the angel started humping him in his sleep. It felt weirdly...good, needy and Castiel moaned in his sleep. Dean gave a fiendish smile, his own morning wood straining between his legs. With much effort Dean pried Castiel off his leg, rolling him over on his side to show the angel's bare ass. They had sex just before they fell asleep and Dean could still see remains of lube and cum streaked across the angel's ass.

Dean wiped some of the remaining lube and gave an experimental prod at the Cas's entrance with his finger. Castiel didn't wake up, good. Dean pressed harder until his finger was enveloped inside the angel's wet heat. Castiel gave a small moan, pushing his ass back but still asleep. _This was kind of fun,_ Dean thought as he slipped another finger in with ease. Cas was so relaxed in his sleep, his muscles compliant and still loose from last night. By the third finger Dean couldn't believe that Castiel was still asleep. His dick ached between his legs and he wanted nothing more than to be inside his angel right now. Shifting position until his chest was pressed against Cas's warm back. Castiel moaned, eyes snapping open as Dean's dick stretched him out.

"D-Dean?" Castiel croaked out, his voice rough from sleep.

"Yes angel?" Dean whispered, pressing gentle kisses to Castiel's shoulder as he started to rock his hips. Cas didn't answer, he only responded with rough moans as Dean's hand slipped around his waist, teasing a finger over the head of his dick. Pants and moans filled the room as Dean stoked Castiel in time with his thrusts until both men came at nearly the same time. _"Dean."_ Castiel gasped out as he rode out his orgsam while Dean thrusted gently through his own.

"Good morning." Dean purred into Castiel's shoulder.

"Mnnn good morning." Castiel smiled, eyes closed as he leaned back to steal a kiss.


	11. K is for Knife Play

**Summary for the Chapter:**

> Knife play-When used in a sexual context it refers to the use of a blade to enhance a sexual experience. Knife play may be used in a variety of ways depending on the individuals sexual preference. It may range from simply showing the knife to instill fear, sensually running the knife along the partner possibly creating light cuts to heighten sensitivity and excitement.

Dean gasped as the cold steel ran along his spine, a slight chuckle from the angel behind him.

"Does that feel good?" Castiel smirked as he ran the hunting knife down between Dean's shoulder blades, down the small of his back and over the swell of his ass. Dean always did like danger, it followed him everywhere and Dean had begun to love it. Dean flinched when the blade nicked a spot on his ass, blood seeping to the surface. "Sorry." Castiel pressed a kiss to the wound, healing it. "Do you want me to keep going?"

"Yeah, s'okay." Dean sighed out, burying his face in the pillow as the blade was dragged across the back of his thigh and over his calf. Dean momentarily humped the bed, this was weirdly relaxing but at the same time very hot. Maybe it was the impending sense of danger, his well as his well-being in Cas's hand, Dean wasn't sure but he didn't really care to figure it out. He moaned when the blade tickled the small of his back, his back arching up.

"Dean." Castiel laid a hand on the small of Dean's back. "Be still or you'll get cut again." Dean complied, laying flat on the bed again as Castiel ran the blade down his neck and traced his shoulder blades. The angel leaned in, turning Dean's head and ghosting the blade over full lips before placing a deep kiss on the hunter. The angel gave him a thoughtful look before rolling Dean onto his back.

Castiel straddled Dean thighs, gripping the knife to bring it down Dean's chest and the hunter gasped out, trying his best not to arch off the bed. The angel traveled lower, dragging it down Dean's abdomen, bringing it uncomfortably close to his manhood.

"Cas..." Dean gave a warning in his voice.

"Don't worry Dean, I know what I'm doing." the angel smiled, brushing the flat of the blade along Dean's dick. Dean let out a sharp breath, gripping the sheets when the back of the blade slid down his inner thigh.

After a few minutes Dean was completely tense, his muscles on edge and his eyes shut tight. He gasped as the blade stayed on the inside of his thigh, his lover's hand now stroking his dick. Dean came with a gasp as the blade gave a small cut to his inner thigh.

Once his cuts were healed, Castiel laid down beside a now breathless Dean and chuckled.

"What?" Dean sighed, blissed out from his orgasm.

"You are so weird." The angel smirked.

"Shut up."


	12. L is for Leather

**Summary for the Chapter:**

> Leather. It's pretty self explanatory.

"Um Dean are you sure I should get these?" Castiel turned awkwardly to look at his ass that was currently clad in tight black leather pants. Castiel's plump ass strained against the leather, his dick almost clearly outlined by the fabric.

"Most definitely." Dean licked his dry lips, eyes hungrily roaming over the angel.

"Okay, just let me change-" Dean grabbed Castiel's arm.

"Wear them out." Dean pulled Castiel and yanked him to the register.

Castiel looked at the cashier then his pants. "Dean how is she supposed to scan them?" Dean ripped the tag off and handed to the cashier. Once they were rung up Dean handed the cashier more money than the pants costed and rush Castiel to the Impala.

"Dean?" Castiel stared at the hunter who was gripping the steering wheel with enough force to almost break it. "Whats wrong?" Cas touched Dean's thigh and the hunter nearly swerved off the road.

"Oh fuck this." Dean pulled over to the side of the road, the angel looking at him questionly. Cas grunted when Dean lunged at him, forcing a kiss that nearly took Cas's breath away.

"Dean w-what are-"

"Those pants Cas. Those fucking pants. Fuck you look good in leather." Dean grunted in irritation at the small space of the front seat. "Backseat." Dean stated and the two men moved to the back, Dean on Cas in less than a second. The men's tongues insistently invaded each others mouths. "Dammit Cas. You're so fuckin' hot." Dean licked the roof of the angel's mouth and Cas moaned as he bucked his hips up. Dean scrambled down to unbutton the tight jeans, forcing them down just enough to free Castiel's erection.

Cas gasped out Dean licked over the head of his dick, hands trailing down the leather blanketing Castiel's thighs. "D-Dean. Oh fuck." Castiel rarely cursed but Dean's tongue always made all his inhibitions disappear. Dean continued to stroke the leather as he took Castiel to the back of his throat. The hunter hollowed out his cheeks. Sucking hard as his lover clawed at the leather seat of the Impala.

"Dean. Dean, _Dean!_ " Castiel's warning was too late as he came down the hunter's throat. Dean licked his lips, Castiel's dick in his hand as he smiled.

"We **_have_** to get you more leather."

 


	13. M is for Mastigophilia (punishment)

**Summary for the Chapter:**

> Mastigophilia- Punishment

Dean rushed to the door the moment he heard it click open, excitedly pouncing his lover. During the day Dean stayed at home, happily keeping up the house while his significant other worked all day, five days a week at a law firm.

"Cas!" Dean grinned playfully, if he had a tail it would be wagging wildly. Cas looked down at his small lover smiling at the twinkle in Dean's beautiful emerald eyes.

"Did you have a good day baby?" Castiel cooed over Dean, gently stroking his short light brown hair. Dean purred and leaned into the touch, continually rubbing his head into Castiel's chest.

"Uh huh." Dean answered, arms going to Cas's back to pull him closer.

"Were you a good boy?" Castiel stopped petting Dean when he felt the smaller man freeze. "Dean..." There was a harsh warning in Castiel's tone and Dean went rigid. He pulled back, Dean's eyes were downcast to the floor, his fingers twiddling nervously.

"Y-Yes." Dean mumbled to the floor.

"Dean." Castiel gripped his lover's chin, pulling him up to lock Dean's green with his blue. "I know when you're lying to me."

"I'm sorry Cas. I wasn't a good boy." A flush of embarrassment highlighted Dean's cheeks and Castiel gave a disappointed sigh.

"Go to the bedroom, strip and lay on your stomach with your face in the pillow until i come in there." Castiel sighed like he was being supremely inconvenienced. Dean did as he was told, hanging his head in shame. Having only been clad in a small pair of blue boyshorts, Dean was able to quickly undress and lay on the bed as Castiel instructed. Five minutes passed, fifteen, twenty. Dean tensed up in anticipation as he waited for his punishment. Not moments later Castiel arrived in their bedroom, having shedded his suit jacket and the sleeves of his dress shirt rolled up to his elbows. Dean flinched when the weight of the bed shifted and a firm hand gently pressed to his bare ass.

"What did you do Dean?" Castiel asked as he gently ran his hand over the swell of Dean's ass. For a minute Dean didn't answer, face still buried in the pillow.  _"Dean."_ Castiel gave a quick swipe against Dean's ass and the smaller man yelped. Dean gulped before answering.

"I-I touched myself while you were at work." Dean mumbled into the pillow. Dean and Castiel had an arrangement, unless given Castiel's permission he was not allowed to touch himself and in return Castiel worshipped Dean, gave him all the intimacy, care and spoiled him rotten. Not to mention to most mind blowing sex.

"How?" Castiel glared, rubbing over Dean's ass again.

"I-I was thinking about you." Dean bit his lip before continuing. "About you kissing me all over, your fingers stretching me out as I moaned your name and stroked myself."

Castiel sighed, hand still stroking over Dean's ass. "I have to punish you Dean."

"I know." Dean mumbled, keeping his face buried in the pillow, arms resting under it. Castiel's hand pulled back and Dean tensed up when he knew what was coming. _Slap._ Dean held back a whine at the stinging on his skin.

"Don't tense up." Castiel growled and Dean relaxed. Dean knew that if he tensed up it would hurt less and Castiel wasn't pleased.  _Slap._ This smack was harder and tears welled up in Dean's eyes."I don't like having to punish you Dean."

"I know." Dean moaned at another strike. Castiel stilled his hand, hovering over Dean's ass.

"You're not supposed to be enjoying this." Castiel frowned, smacking Dean's ass again. Dean moaned again and started humping the mattress.

"Dean!" Castiel smacked Dean again and again Dean moaned. Dean whined when Castiel pulled him up by his hair. "Did you not get enough earlier?" Castiel's hand moved between Dean's cheeks, teasing at his puffy entrance, still wet from earlier. Dean gasped as Castiel slipped a finger in easily, stroking Dean's warm inner walls.

"Cas. Cas." Dean chanted his lover's name over and over.

"You're a bad boy Dean." Castiel slipped another finger in, grazing over Dean's prostate. "Apologize and I'll let you get off." Dean moaned, furiously humping the bed and fucking himself back on Castiel's fingers.

"I-I'm sorry." Dean whined, Castiel abusing his sweet spot until he came all over the bed.

"Good boy." Castiel pulled his fingers free before placing a gentle kiss on Dean's sweaty forehead. Dean smiled weakly in response.

"I promise I won't be bad anymore." Dean bit his lip, giving Castiel those puppy eyes he knew his lover couldn't resist.

"It's okay baby, I forgive you." Castiel smiled, placing a chaste kiss to Dean's lips.


	14. N is for Name-Calling.

**Summary for the Chapter:**

> Finally put N up lol.

"Like that don't you bitch?" Castiel growled as he slammed into Dean so roughly the head board shook.

"Yes. Fuck yes." Dean labored out as he gripped the worn pillow in front of him. He whined as Castiel gripped his hair and tugged tight.

"Who's bitch are you? Who do you belong to?" Castiel growled out as he gripped Dean's hips with his free hand pounded into him hard and fast.

"Y-you Cas...only you!" Dean moaned as he pushed his ass back to meet Castiel's thrusts.

"Damn right. You're my whore. Only mine." Castiel bit down hard on Dean's shoulder and the Hunter cried out painting the bed below him. Castiel felt Dean clench around him and released inside the Hunter. 

"Dean I don't understand why you want me to talk to you like that during sex." Castiel commented as he snuggled into Dean's arms a few minutes later.

"It just turns me on Cas." Dean answered, both eyes closed."

"Why?" Castiel asked innocently as if he hadn't just called Dean a bitch and a whore a few minutes ago.

"Just go to sleep Cas." Dean grumbled.

"Assbutt." Castiel spoke below him, Dean smirked before drifting off.


	15. O is for Omega

**Summary for the Chapter:**

> Male Omegas are self-lubricating and have the ability to become pregnant, sometimes referred to as being bred or mated. Lovers may form pair-bonds with a special connection with telepathic or empathetic qualities. Paired Alphas may be jealous and possessive of their mate, while the Omega may become submissive. Omegas and Alphas may go into heat and need to have sex; this may be the only time Omegas are fertile.
> 
> I also tried to put a little biting kink in there :3 (odaxelagnia)

"Hey baby." Dean gave a small smile as he wrapped his arms around Castiel while his mate was doing dishes.

"Hello Dean." Castiel smiled, craning his neck to steal a kiss while he was forearm deep in now chilling soapy water. "How was work?"

"Good." Dean answered as he peppered kisses along his mate's neck and the omega sighed with content. "But all I wanted all day was to come home to my beautiful mate." Dean's hands roamed all over Castiel's body, slinking under his tee and rubbing Cas's cut hips.

"De-Dean" Castiel laughed as Dean assaulted his neck rapidly with fevered kisses. "I'm trying to do the dishes."

"The dishes can wait." Dean commented as he gave a small nibble at Cas's shoulder. The omega was clad in a pair of blue jean shorts and a black AC/DC tank top, Dean sliding the sleeves down to get better access to his neck.

"Mnnn, Dean." Castiel sighed out, arms going lax in the dishwater as Dean nibbled over his claim mark. Castiel gasped as Dean opened his mouth wide, a sharp pain in his shoulder as Dean bit over the healed mating mark and he moaned. "Nghh Dean." Castiel's legs went weak, pressing weight back on his alpha. Dean gasped out as he released his omega's shoulder, licking over the bite.

"Wanna have sex in the kitchen?" Dean asked as he nosed Cas's shoulder.

"Absolutely." Castiel breathed out.

Castiel's arms were still soaked as Dean bent him over the counter and gently nibbled his omega's ass. "Dean." Castiel whined while slick dripped down his thighs, bucking back as Dean licked his slick entrance.

"Mnn Cas, you taste so good." Dean ran his tongue along his mate, licking his lips at the taste. When Dean had met Castiel in the bookstore he caught the sweet scent of apple pie when their eyes met, later learning it was the scent of his potential mate's arousal. Four years later Cas still tasted like apple pie. 

"Deaaaan." Castiel whined pushing his ass back when Dean slipped his tongue in. "Please. Stop teasing me." Dean pulled back, licking his lips one final time before standing up, unbuckling his pants, and sliding into his mate with ease. 

"Fuck, Cas." Dean sighed, nestling deep inside his lover. He started with slow thrusts, bunching up his and Cas's shirt and moaning at the skin on skin contact. "God baby, you feel so good." Dean pressed a kiss to the omega's neck and his mate whined.

"What's wrong babe?" Dean stopped kissing, stilling himself. 

"H-Harder. Please." Castiel whined, pushing his ass back, his face turning pink. Dean smiled, rocking his hips again in a much faster pace. Castiel panted underneath him, crying out when Dean bit over his mating mark. 

"Dean. Dean. Deaaaaan." Castiel whined out, pushing back to meet Dean's thrusts as he came all over the counter. A few fevered thrusts later Dean tied himself to his mate, filling him up.

Dean licked the fresh wound on his mate's neck before snuggling into his shoulder.

"Mnnn, I love you." Dean ran a hand over Castiel's own.

"I love you too." Castiel smiled, keeping propped on the counter as he looked over at the sink. "The dishwater is cold."

"Fuck it." Dean mumbled sleepily into his mate's neck.


	16. P is for Priest Kink

"Ah fuck...father." Dean moaned out as the priest grinded against his ass.

"Confess your sins Dean." Father Castiel spoke as he continued to rock his hips and tug at Dean's cropped hair.

"I-I..." Dean bit his lip, moaning when Castiel reached his free hand over to stroke Dean through his jeans.

"Tell me Dean. All your sinful thoughts, the things that you want me to do to you." The priest drove his point home with a harsh thrust against Dean.

"I-I want you to touch me." Dean could practically feel the blush creeping into his cheeks. "I want you to fuck me, tell me that I'm a filthy sinner and how bad I am." Dean gasped when the priest shucked his jeans down, a slight chuckle came from behind as Castiel fingered pink laced panties that barely covered Dean's ass.

"Oh my." Castiel smirked running his fingers along the waistline of the panties. "You really are a dirty one Dean." Dean's face managed to get redder as the priest smoothed his hands over the pink satin.

"I'm going to fuck you with these on." Castiel smirked as he thoughtfully skimmed the panties with his finger. At those words Dean's cock twitched, already peeking out over the waistline of the panties.

"Fuck yes. Please." Dean begged, pushing his ass back to egg the holy man on. His breath hitched when he felt the panties pushed to the side and the priest's warm tongue practically worshipping his entrance. Within minutes Dean was bucking wildly, threatening to move the church pew from its designated spot. "Please Cas. Fuck me, please."

"So fucking filthy." Castiel cursed, puncuating with a quick swipe of his tongue. "You're such a filthy fucking sinner Dean. Laid out for me like this, begging a holy man to fuck you." Dean moaned at Castiel's words and began humping the air.

"Pleeease." Dean begged again and Castiel smiled.

"Well if you want it that badly." Dean gasped as the priest slid into him torturously slow, inch by inch.

"F-Fuck." Dean moaned out as Castiel gave him a moment to adjust.

"Mnn Dean. You feel so good." Castiel threw his head back before grabbing Dean's hips and pumping in and out of him with quick shallow thrusts.

"Father...fuck...Cas-Ah!" Dean cried out as the priest struck his prostate and his legs went limp. The only thing keeping him up were Castiel's hands tightly gripping his hips. The priest assaulted the same spot over and over Dean nearly ready to tip over the edge.

"Like that don't you Dean?" Castiel leaned in close to Dean's ear. "Like it when I fuck a filthy sinner like you?" And just like that Dean went over the edge, moaning out his orgasm as he painted the pew and stained his panties. Castiel came only two thrusts after, thrusting Dean through his orgasm.

Once Castiel was dressed he looked over to see Dean collapsed on the pew, covered in sweat and cum.

"Come here my child." Castiel pulled a rag from his pocket and wiped Dean clean and redressed him.

"Go home Dean." Castiel kissed the top of his head and the other man sighed with content. "I'll see you next Sunday."

**Notes for the Chapter:**

> And panties. I had to have panties in there lol.
> 
> (And I know I know I need to do "N" lol.)


	17. Q is for Quiet

**Summary for the Chapter:**

> Omg I finally thought of something for Q.

They weren't being as quiet as Dean had hoped. Each breathy moan that Castiel gave as Dean fucked him against the desk just became louder and louder. And while it was beyond hot, they were going to get caught.

As Castiel let out a high moan and wrapped his legs around Dean's back the Hunter groaned at the contact. "Cas-fuck-be quiet or we're gonna get caught." They were on a case and the horny angel just couldn't wait to get out of the police station for Dean to fuck him. So here they were in an unused office trying thier best not to get caught. Well, Dean was at least.

"Nggh I can't help it Dean." Castiel grunted as he grasped Dean's shoulders as his lover thrusted harder into him. "Feels so fucking good." Castiel trying to at least keep his talking to a whisper. Dean moaned, every time the angel cursed it usually drew some kind of noise from Dean.

"Well keep quiet somehow." Dean managed to protest as the angel clenched around him. Castiel panted and locked eyes with Dean before leaning forward and biting hard into the Hunter's neck. Dean gave out a strangled moan and Castiel's moan muffled through the bite. The bite hurt, it stung somehow but fuck did Dean love it. A few thrusts later Dean came inside the angel and jacked Castiel two times before he spilled all over Dean's hand.

"Fuck Cas." Dean sighed, burying his head in the angels shoulder. "What a way to keep quiet." Castiel chuckled in response before both men cleaned up and exited the empty office grinning.

**Notes for the Chapter:**

> You know what gets the rest of the alphabet written? Reviews lol. Seriously guys it makes me write more and faster lol.


	18. R is for Rimming

**Summary for the Chapter:**

> I feel like rimming is pretty self explanatory lol.

"Ah fuck...Cas" Dean's fingers knotted into the worn motel sheets underneath him. One thing was for sure, he was glad Sam decided on his own room. Castiel hummed approvingly against Dean's ass as he licked him open.

"Ease up Dean." Castiel murmured, both hands grasping Dean's tense muscular thighs to keep him a place. Dean moaned as Castiel gave a quick swipe of his tongue and tried to relax his muscles. Eventually the angel got Dean relaxed enough to plunge his tongue inside and the Hunter gave out a strangled groan.

"Fuck. Fuck." Dean grinded his teeth, gripping the sheets tighter as the angel began to roughly fuck him with his tongue. Dean was practically mewling from the pleasure but stopped when one of the angel's hands left his thigh. "Cas what are you? Ah...oh." Dean moaned again as Castiel stroked his dick and continued to eat out his lover. Castiel pulled his mouth away for a moment and Dean instinctively pushed his ass back searching for more.

Castiel leaned into Dean's ear and whispered as he stroked the hunter's cock. "Do you think you can come just from my tongue Dean? Can you do that for me?" The angel's words sent a shiver up Dean's spine and he furiously nodded his response.

"Good boy." Castiel breathed into his ear before releasing Dean's dick and going back to opening him up. The angel pushed his tongue in and out at a rapid pace, Dean shook and jolted under him trying his best not to wake the entire motel. Castiel curled his tongue up inside and Dean was done, coming all over the sheets from one of the most intense orgasms of his life. He collapsed on the cum stained sheets and felt Castiel climb behind him and put his chest to Dean's back. After a moment Dean spoke.

"Sam is definitely getting a seperate room from now on."

**Notes for the Chapter:**

> I also wrote the chapter N is for Name calling so you can go back and read that if you like ^^.


	19. S is for Spanking

Fifteen. Around fifteen was when Castiel's ass began to sting.

"You want me to stop babe?" Dean asked as his hand hovered over Castiel's cherry red skin.

"No. Don't stop." Castiel begged into the pillow underneath him and winced at the sixteenth slap.

Dean's dick had been trying to practically tear through the denim since slap number two. The way Castiel keened and moaned at every strike might just have been the sexiest thing Dean has ever experienced.

Four slaps later Castiel was desperately humping the bed, his cock aching for touch.

"Dean..." Castiel whined into the pillow and gripped the sheets from one more swing.

"I got you babe," Dean placed soothing kisses along Castiel's sore skin before moving his hand to his dick. Dean jacked Castiel slowly as he grinded his clothed dick against Castiel's soft skin. 

Castiel's breath became ragged and heavy as Dean gave two more tugs and three more slaps before he came undone. "Dean!" Castiel screamed into his pillow. 

"Fuck! Cas!" Dean rutted into Castiel twice before coming in his pants like a teenager. He didn't realize how hot he found spanking Cas.

"That feel good?" Dean asked as he rubbed aloe on his lover's skin. Castiel hummed his approval as Dean eased the pain and massaged his ass.

A few minutes later Castiel had fallen asleep and Dean awkwardly shifted off their bed to go change his pants.

**Notes for the Chapter:**

> It uh turned out sweeter than I intended.


	20. T is for Teasing

**Summary for the Chapter:**

> Sorry for the delay guys. Finally my brain worked again. The letter U is going to be under age with teacher Cas and teen student Dean :).
> 
> Also thank you to everyone who gave suggestions :3.

Dean groaned as Castiel nudged his shoulder, twice, before the other man gave up and went into the kitchen to get breakfast.

The moment Dean heard their bedroom door close, he hopped up from the bed and immediately began to rifle through his dresser. He'd been awake for the past hour, waiting for Cas to leave. Dean chuckled as he pulled a lacy pink thong from the bottom of his dresser. Cas had spent hours teasing Dean the night before during sex, and Dean intended to return the favor. He sighed as he slowly slid the soft fabric of the panties over his ass. It was one of the best feelings in the world. Cas knew about his panty kink, of course. They'd begun dating shortly after Cas became human, and that had been six months ago. Cas had found Dean's panties the first week.

The sight of Dean in panties always drove Cas crazy, and Dean intended to use that to its full advantage today.

After dressing the rest of the way, Dean headed to the kitchen where Cas and Sam were eating breakfast.

"Hey, guys!" Dean belted, a grin spreading across his face. Sam cocked an eyebrow at Dean's cheerfulness and Cas smiled.

"Good morning, Dean," Castiel greeted him as Dean strolled over and planted a kiss on Cas's cheek.

"Mornin', babe," Dean smiled and sat down to the plate Cas had made for him. Sam gagged and Dean shot him a playful glare. Their relationship wasn't a secret and Sam had no problem teasing them about it.

"So, we should go out today," Dean piped up. "The three of us."

"I'm down," Sam answered.

"Sounds good," Cas smiled at Dean again.

Their first stop was the grocery store. They were low on beer and snacks. Dean squatted down to reach something on the bottom shelf just as Cas rounded the corner into the aisle.

Dean heard a sharp intake of breath from behind him and smirked to himself.

"Everything okay, Cas?" Dean smiled innocently. He knew his thong was peeking up over the waistband of his jeans, and he couldn't help but notice how red the ex-angel's face was.

Cas was about to open his mouth when Sam rounded the corner, and Dean quickly stood up.

"Hey, guys," Sam greeted them with an armful of what Dean still referred to as "rabbit food".

"Hey, Sammy. You ready to go?" Dean cradled his own purchases while Cas, still dumbstruck, stood in the middle of the aisle.

The three of them checked out and Cas stayed silent. Sam didn't seem to notice, considering Cas usually wasn't talkative, anyway.

Their next stop was to get gas. Sam went inside for some snacks while Dean leaned over unnecessarily to put gas in the Impala.

"Dean."

A gravel-deep voice spoke behind Dean, and the hunter felt a hand on his shoulder.

"Yeah, Cas?" Dean turned his head and gave a huge grin. The ex-angel was staring directly at the pink lace riding over Dean's jeans.

"Why are you—" Cas was interrupted by Sam's reappearance as he headed back towards the car. Cas removed his hand and climbed into the back seat before Sam reached the Impala.

Later that night Dean insisted they play pool and have a few drinks. They stopped at a seedy bar not far from the bunker.

Sam and Cas were drinking together at the bar while across the room Dean was hustling some pool.  
Cas glanced over just in time to see Dean's jeans ride far too low as he bent over the pool table. Cas inhaled heavily as the denim rode low enough to show the thin strip of fabric nestled between Dean's ass cheeks.

"Cas, what are—" Sam started to say as Cas hopped off of the bar stool.

The ex-angel yanked Dean back by his collar, away from the pool table, and dragged him out the door. Sam sat there, frozen with surprise. He decided it probably wasn't a good idea to follow.

Dean let out a breathy laugh as Cas all but slammed him into the alley behind the bar. Cas may not have been an angel anymore, but he was far from weak.

"Well, hello there, angel," Dean practically purred. The nickname still fit.

"Dean..." that thick, gravelly voice struck Dean's ears and his dick began to fill.

"Why are you teasing me?" Cas pressed his body against Dean's, grazing his lips along the shell of the hunter's ear.

"Mmm, 'cause it's fun," Dean smirked and then moaned as Cas bit his ear on the wrong side of too-hard.

"You think it's fun," Cas growled into Dean's ear as he slipped his hand down the front of Dean's pants, “to get me all riled up."

Cas gripped Dean's cock through the thin fabric.  
  
"All day. With your brother present."

Cas stroked Dean through the panties and undid his pants with the other hand.

"Where anyone could see those panties that are meant just for me?"

Cas gripped Dean's dick, hard, and the hunter let out a strangled groan.

"Yes," Dean breathed out in answer, thrusting against Cas's palm like a dog in heat. Dean heard a car go by outside the alley but barely registered the sound as his blood pounded in his ears.

Cas slipped a hand under the panties and began furiously jacking Dean off as the ex-angel bit and licked at his neck.

"F-Fuck Cas, I'm—" Dean let out a pained whine as his lover abruptly pulled his hand free, denying Dean his release.

Cas pressed a palm to Dean's erection as he spoke into his ear calmly, "We are going to stay here another hour and a half. That will give you time to think about the next time you're tempted to tease me again. Then, I'm going to fuck you so hard, and make you moan and scream so loudly, that Sam has to go to the next state to avoid hearing us. Understand?"

Dean whimpered and nodded hastily as Cas pulled his hand away and headed back into the bar.  
Dean buttoned his pants and quickly followed.

The next hour and a half was spent hiding his erection and squirming under Cas’s steely glare.

 


	21. U is for Underage

**Summary for the Chapter:**

> I decided on a teacher/student fic because that is my jam.
> 
> Dean is 16 and Cas is 30.
> 
> Hope you like it :).

Dean was pretty sure his history teacher was talking. Well, he heard that gravel, sex laced, voice resonating in his ears but he wasn't sure exactly what he was saying. Dean scanned his teacher, from his mussed, black sex hair, strong jaw, to that lean runner's build under that tight white dress shirt.

"Mr.Winchester? Mr.Winchester!"

Dean snapped out of his dazed state and realized fierce blue eyes were locked with his green.

"Oh uh...sorry Mr.Novak," Dean stuttered and his teacher pulled back.

"Dean, maybe you can tell us the year the Declaration of Independence was signed?"

The teacher cocked an eyebrow as the rest of the class giggled.

"Uh 1976?" Dean blurted out. The entire class busted into laughter and Mr.Novak shut them up with a glare.

"Mr.Winchester, you will stay after class," The teacher sighed and went back to his lesson.

After class was over, Dean stayed at his desk and waited until the last student had left. Dean tensed up in his seat as Mr.Novak locked the door and returned to lean against his own desk.

"Well, Dean. Why weren't you paying attention in class?" The teacher crossed his arms and glared at his student.

"I was distracted," Dean smirked.

"By what exactly?" The older man cocked an eyebrow.

"That perfect ass of yours." Dean grinned and his teacher held back a smile.

"What am I going to do with you?" The man sighed and pinched the bridge of his nose.

"Aw come on Cas," Dean rose from his desk and closed in on Cas, wrapping his arm's around the man's neck. "You know you love me."

"Unfortunately." Cas sighed as he gripped Dean's ass.

"Unfortunately? That hurts my feelings," Dean pouted and nuzzled Cas's chest.

"Would it make you feel better if I fucked you on my desk?" Cas rubbed his growing hard-on against Dean's front.

"Mmm definitely," Dean purred and pushed back against Cas.

Cas shoved Dean's pants around his ankles before lifting him onto the desk. "My next class is in fifteen minutes," Cas spoke as he rifled through his desk drawer for lube.

"Mmm better fuck me quick then," Dean purred and gripped Cas's shoulders.

"Such a mouth. Won't have much time to prep you," Cas mumbled into Dean's ear as he slipped one finger into the teen.

"S'okay. I can take it," Dean pushed down on Cas's finger.

"Okay, you have to be quiet," Cas grabbed a condom from his pocket, and shoved his pants down. Cas rolled the condom on and pushed against Dean's entrance.

"Fuck!" Dean bit out and Cas covered his mouth. Dean whimpered as Cas pushed in swift and hard.

"Phugk," Dean bit out from under Cas's hand. Dean gripped Cas's shoulders hard enough to bruise as his teacher immediately set a punishing pace.

The desk rocked under them as Cas plowed hard into the young man. "Mmmn, Dean. Fuck you feel so good, my good boy."

"Mmm yeah Cas. Just for you," Dean moaned and threw his head back.

Cas leaned forward to brace his hands on the desk and pounded into Dean harder.

"Fuck, Cas, right there. Oh god," Dean shook his jeans off and dug his heels into Cas's back. Dean bit his lip to silence a moan as he came between their stomachs.

"Mmm, so good." Cas buried his nose in Dean's neck as he shuddered through his own orgasm seconds later. Dean chuckled as he buried his face into Cas's neck.

Cas looked up at the clock on the wall and sighed. "My class will be here in four minutes. And two of them are always early."

Cas pulled out, tied the condom and stuffed it in his pocket. "Better get dressed."

Dean hopped off the desk and gathered his pants from the floor. Just as Dean buckled his belt there was a knock at the door. Cas unlocked the door and as he said, two students filed in.

"That will be all Mr.Winchester. Pay attention in class from now on," Cas motioned to the door. Cas held back a smirk as Dean walked awkwardly toward the door.

"Yes, Mr.Novak," Dean winked before exiting the classroom.

**Notes for the Chapter:**

> Hope it's okay, I updated so fast. Also I need a lot of ideas for the letter V. Let me know if you guys have any ideas.


End file.
